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Preparation method of alkyl arabinoside

A technology of arabinoside and arabinose, applied in the field of preparation of alkyl arabinoside, can solve the problems of difficult separation of product and catalyst, deepened product color, complicated operation steps, etc., and achieves the effects of low production cost, convenient operation and simple process

Inactive Publication Date: 2010-06-30
EAST CHINA NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are many deficiencies in these methods. Although liquid acid is used as a catalyst, although the catalytic activity is high, it is easy to corrode equipment, and some acids also have side reactions with raw materials, resulting in darker product color, and separation of product and catalyst in the post-treatment process. Difficult, resulting in cumbersome operation steps
[0003] At present, there is no report on the synthesis reaction of alkyl glycosidation with other monosaccharides

Method used

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  • Preparation method of alkyl arabinoside
  • Preparation method of alkyl arabinoside

Examples

Experimental program
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Effect test

Embodiment 1

[0017] a. Synthesis of fully acylated decyl arabinoside

[0018] Take 10g of fully acylated arabinose, mix 6.0ml of n-decyl alcohol (Acros) and 100ml of anhydrous dichloromethane, stir at 0°C and add 3.0mL of trimethylsilyl trifluoromethanesulfonate (TMSOTf) (Aldrich) , then heated to 25°C and continued to stir, and carried out the full acylation reaction for 3 hours. After the reaction, separated by column chromatography to obtain 5.99 g of pure white solid, which was full acylated decanyl arabinoside, and its yield was 45%. (α:β≈1.7:1).

[0019] NMR structure analysis of fully acylated decanyl arabinoside was carried out, and the test data are as follows:

[0020] 1 H NMR (500MHz, CDCl 3 ), δ: 0.88(t, 3H, CH 3 ), 1.20-1.32(m, 14H), 1.54-1.60(m, 2H), 2.03, 2.07, 2.14(s, 9H, 3COCH 3 ), 3.46(m, 1H), 3.63(m, 1H), 3.86(m, 1H), 4.03(m, 1H), 4.40(m, 1H), 5.03(m, 1H), 5.20(m, 1H) , 5.26 (brs 1H).

[0021] b. Synthesis of Decyl Arabinoside

[0022] Take 2g (4.8mmol) of the ab...

Embodiment 2

[0029] a. Synthesis of fully acylated nonyl arabinoside

[0030] Mix 1 g of fully acylated arabinose, 0.6 ml of nonanol (Acros, 97%) and 40 ml of anhydrous toluene, stir at room temperature and add 1.0 mL of boron trifluoride ether (chemically pure), then heat to 50°C and continue stirring. The full acylation reaction was carried out for 5 hours. After the reaction, the pure white solid was separated by column chromatography to obtain 0.45 g of full acylated nonyl arabinoside, and the yield was 35% (α:β>19:1).

[0031] b, the synthesis of nonyl arabinoside

[0032] Take the above-mentioned fully acylated nonyl arabinoside 0.45g (1.1mmol) and add 1.5ml of anhydrous methanol to mix, stir slowly at room temperature and add 0.12mol L·L -1 MeONa / MeOH solution 0.3ml, carry out deacylation reaction 1 hour, drop Dowex-50 resin (H + , ~5g) neutralized to pH=7, then filtered, and the filtrate was suspended and evaporated under reduced pressure to remove methanol, and the white pure so...

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Abstract

The invention discloses a preparation method of alkyl arabinoside, which is characterized in that the method comprises the following steps: firstly, mixing fully-acetylized arabinose and nonanol or decatyl alcohol with a solvent; then, synthesizing the fully-acetylated alkyl arabinoside under the effect of glycosidation catalysts; and next, obtaining the alkyl arabinoside through deacylation reaction. The invention has the advantages of simple process, convenient operation, high yield, low price and easy acquisition of the synthesis use materials, low production cost and no environment pollution, and in addition, the product has the advantages of good surface activity, no peculiar smell and stable performance, and belongs to a surface active agent with wide application prospects.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to a method for preparing alkyl arabinosides. Background technique [0002] Alkyl glucoside is a new type of non-ionic surfactant developed in recent years. It is known as a "world-class" surfactant and is a new generation of mild, green and environmentally friendly surfactants. Alkyl glycosides are made from renewable resource carbohydrates and long-chain natural fatty alcohols. The raw materials used in the entire production process are cheap and easy to obtain, and there are no other toxic and harmful wastes in the production process except for the products. Produce (Wang Peiyi, Xu Baocai, Wang Jun: Surfactant—Synthesis·Performance·Application. Beijing: Chemical Industry Press, 2007). Active agent. [M]. Beijing: Chemical Industry Press, 2003.), most of the current patent reports use glucose as raw material to synthesize alkyl glycosides, such as CN200510096464.8, CN988131...

Claims

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Application Information

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IPC IPC(8): C07H15/04C07H1/00
Inventor 张剑波陈旋李娟张博
Owner EAST CHINA NORMAL UNIV
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